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Heterocyclic synthesis via enaminones: Novel synthesis of (1 H )‐pyridin‐2‐one, pyrazolo[1,5‐ a ]pyrimidine and isoxazole derivatives incorporating a N ‐methylphthalimide and their biological evaluation
Author(s) -
AlOmran Fatima,
ElKhair Adel A.
Publication year - 2005
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570420222
Subject(s) - chemistry , isoxazole , malononitrile , moiety , hydrazine (antidepressant) , pyrimidine , antimicrobial , hydrate , proton nmr , carbon 13 nmr , hydroxylamine , aspergillus niger , sonogashira coupling , condensation reaction , cyanoacetamide , medicinal chemistry , organic chemistry , combinatorial chemistry , stereochemistry , catalysis , palladium , biochemistry , chromatography
Abstract Novel synthesis of (1 H )‐pyridin‐2‐one, pyrazolo[1,5‐ a ]pyrimidine and isoxazole derivatives incorporating N ‐methylphthalimide moiety are reported. Reaction of enaminone 2 with malononitrile affords 4. Condensation of 2 with cyanothioacetamide or benzoylacetonitrile affords compounds 6 and 7 respectively. Reaction of 2 with hydrazine hydrate afford 2,3‐dihydrophthalazine‐1,4‐dione ( 10 ). Condensation of 2 with hydroxylamine and 3‐aminopyrazole derivatives affords compounds 12 and 15a,b respectively. Antimicrobial and antifungal activity were determined for representative compounds and most of them showed moderate activity as antimicrobial agents, while compounds 2 and 7 show strong activity against Aspergillus niger. The structure of the newly synthesized compounds was elucidated by elemental analyses and 1 H nmr spectra and some cases by 13 C nmr investigation.